{[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3S)-3-hydroxy-3-({2-[(2-{[(3R)-3-hydroxybutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

• ChemBase ID: 3271
• Molecular Formular: C25H42N7O18P3S
• Molecular Mass: 853.623363
• Monoisotopic Mass: 853.15198843
• SMILES: C[C@@H](O)CC(=O)SCCNC(=O)CCNC(=O)[C@@H](O)C(C)(C)CO[P@@](=O)(O)O[P@](=O)(O)OC[C@@H]1O[C@H]([C@H](O)[C@H]1OP(=O)(O)O)n1cnc2c1ncnc2N
• Canonical SMILES: C[C@H](CC(=O)SCCNC(=O)CCNC(=O)[C@H](C(CO[P@](=O)(O[P@@](=O)(OC[C@@H]1O[C@H]([C@@H]([C@H]1OP(=O)(O)O)O)n1cnc2c1ncnc2N)O)O)(C)C)O)O
• InChI: InChI=1S/C25H42N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-14,18-20,24,33,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,14+,18-,19+,20-,24-/m1/s1
• InChIKey: QHHKKMYHDBRONY-XQUJUNONSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2S,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3S)-3-hydroxy-3-({2-[(2-{[(3R)-3-hydroxybutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: @3-hydroxybutyryl-coenzyme A
• Synonyms: 3-Hydroxybutyryl-Coenzyme A

Database IDs

• PubChem SID: 160966713; 46509071
• PubChem CID: 46936728

CALCULATED PROPERTIES

JChem

• Acid pKa: 0.8136794
• H Acceptors: 18
• H Donor: 10
• LogD (pH = 5.5): -10.663183
• LogD (pH = 7.4): -12.307203
• Log P: -7.138871
• Molar Refractivity: 183.0284 cm^3
• Polarizability: 73.04938 Å^3
• Polar Surface Area: 383.86 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.62
• LOG S: -2.32
• Solubility (Water): 4.07e+00 g/l

DETAILS

DrugBank - DB03612

Drug information: experimental